Shuang-Shuang Xie , Xiang Yu , Qi-Mei Tie , Jing-Ke Zhang , Bei-Bei Zhang , Meng-Nan Zeng , Xiao-Ke Zheng , Wei-Sheng Feng . Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim[J]. 应用天然产物, 2025 , 15(4) : 31 -31 . DOI: 10.1007/s13659-025-00510-1

[1] Badshah SL, Faisal S, Muhammad A, Poulson BG, Emwas AH, Jaremko M. Antiviral activities of flavonoids. Biomed Pharmacother. 2021;140: 111596.
[2] Ullah A, Munir S, Badshah SL, Khan N, Ghani L, Poulson BG, Emwas A-H, Jaremko M. Important flavonoids and their role as a therapeutic agent. Molecules. 2020;25(22):5243.
[3] Maleki SJ, Crespo JF, Cabanillas B. Anti-inflammatory effects of flavonoids. Food Chem. 2019;299: 125124.
[4] Jucá MM, Cysne Filho FMS, de Almeida JC, Mesquita DdS, Barriga JRdM, Dias KCF, Barbosa TM, Vasconcelos LC, Leal LKAM, Ribeiro JE, Vasconcelos SMM. Flavonoids: biological activities and therapeutic potential. Nat Prod Res. 2018;34(5):692-705.
[5] Pietta P-G. Flavonoids as antioxidants. J Nat Prod. 2000;63:1035-42.
[6] Shi S, Li J, Zhao X, Liu Q, Song S-J. A comprehensive review: Biological activity, modification and synthetic methodologies of prenylated flavonoids. Phytochemistry. 2021;191: 112895.
[7] Chen X, Mukwaya E, Wong M-S, Zhang Y. A systematic review on biological activities of prenylated flavonoids. Pharm Biol. 2013;52(5):655-60.
[8] Molčanová L, Janošíková D, DallAcqua S, Smejkal K. C-prenylated flavonoids with potential cytotoxic activity against solid tumor cell lines. Phytochem Rev. 2019;18(4):1051-100.
[9] Šmejkal K. Cytotoxic potential of C-prenylated flavonoids. Phytochem Rev. 2013;13(1):245-75.
[10] Hsueh T, Wu Y-T, Lin L-C, Chiu A, Lin C-H, Tsai T-H. Herb-drug interaction of epimedium sagittatum (Sieb. et Zucc.) maxim extract on the pharmacokinetics of sildenafil in rats. Molecules. 2013;18(6):7323-35.
[11] Ma H, He X, Yang Y, Li M, Hao D, Jia Z. The genus epimedium: an ethnopharmacological and phytochemical review. J Ethnopharmacol. 2011;134(3):519-41.
[12] Li W, Wang L, Chu X, Cui H, Bian Y. Icariin combined with human umbilical cord mesenchymal stem cells significantly improve the impaired kidney function in chronic renal failure. Mol Cell Biochem. 2017;428(1-2):203-12.
[13] Chen X-J, Tang Z-H, Li X-W, Xie C-X, Lu J-J, Wang Y-T. Chemical constituents, quality control, and bioactivity of Epimedii Folium (Yinyanghuo). Am J Chin Med. 2015;43(05):783-834.
[14] Li J, He Y, Zheng X, Li S, Wu Y, Shi W, Pan K, Sun J, Wang Z, Xu J, Zheng X. Flavonoids and prenylhydroquinones from the prepared folium of Epimedium sagittatum Maxim and their inhibition against phosphodiesterase5A. Fitoterapia. 2023;168:105465.
[15] Huong NT, Son NT. Icaritin: a phytomolecule with enormous pharmacological values. Phytochemistry. 2023;213: 113772.
[16] Seyedi Z, Amiri MS, Mohammadzadeh V, Hashemzadeh A, Haddad-Mashadrizeh A, Mashreghi M, Qayoomian M, Hashemzadeh MR, Simal-Gandara J, Taghavizadeh Yazdi ME. Icariin: a promising natural product in biomedicine and tissue engineering. J Funct Biomater. 2023;14(1):44.
[17] Wei J-J, Zhang J-K, Li M, Xie S-S, Tao S-Q, Yang Y, Yang M, Zhu D-H, Zheng X-K, Feng W-S. A new flavonoid glycoside from Epimedium sagittatum. Acta Pharm Sin. 2023;58:180-5.
[18] Xie SS, Zeng MN, Zhang JK, Liu JJ, Wei JJ, Wang R, Li M, Hao ZY, Ji BY, Zheng XK, Feng WS. Epimesatines A-I, nine undescribed prenylated flavonoids with SPHK1 inhibitory activities from Epimedium sagittatum maxim. Phytochemistry. 2022;202: 113314.
[19] Hiep NT, Kwon J, Hong S, Kim N, Guo Y, Hwang BY, Mar W, Lee D. Enantiomeric isoflavones with neuroprotective activities from the fruits of Maclura tricuspidata. Sci Rep. 2019;9(1):1757.
[20] Slade D, Ferreira D, Marais JPJ. Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. Phytochemistry. 2005;66(18):2177-215.
[21] Frelek J, Klimek A, Ruskowska P. Dinuclear transition metal complexes as auxiliary chromophores in chiroptical studies on bioactive compounds. Curr Org Chem. 2003;7:1081-104.
[22] Zheng X, Li W, Ren L, Liu J, Pang X, Chen X, Kang D, Wang J, Du G. The sphingosine kinase-1/sphingosine-1-phosphate axis in cancer: Potential target for anticancer therapy. Pharmacol Ther. 2019;195:85-99.
[23] Yang QQ, Yang Y-F, Chen X-Q, Li R-T, Zhang Z-J. Flavonoids from the aerial parts of Sophora tonkinensis and their potential anti-inflammatory activities. Chem Biodivers. 2024;21: e202400399.
[24] Nur EAM, Yousaf M, Parveen I, Hafizur RM, Ghani U, Ahmed S, Hameed A, Threadgill MD, Al-Rehaily AJ. New flavonoids from the Saudi Arabian plant Retama raetam which stimulates secretion of insulin and inhibits alpha-glucosidase. Org Biomol Chem. 2019;17(5):1266-76.
[25] Nakashima K, Miyashita H, Yoshimitsu H, Fujiwara Y, Nagai R, Ikeda T. Two new prenylflavonoids from Epimedii Herba and their inhibitory effects on advanced glycation end-products. J Nat Med. 2016;70(2):290-5.
[26] Górecki M, Jabłońska E, Kruszewska A, Suszczyńska A, Urbańczyk-Lipkowska Z, Gerards M, Morzycki JW, Szczepek WJ, Frelek J. Practical method for the absolute configuration assignment of tert/tert 1,2-diols using their complexes with Mo₂(OAc)₄. J Org Chem. 2007;72:2906-16.
[27] Di Bari L, Pescitelli G, Pratelli C, Pini D, Salvadori P. Determination of absolute configuration of acyclic 1,2-diols with Mo2(OAc)4 1 Snatzke’s method revisited. J Org Chem. 2001;66:4819-25.
[28] Frelek J, Ikekawa N, Takatsuto S, Snatzke G. Application of [Mo₂(OAc)₄] for determination of absolute configuration of brassinosteroid vic-diols by circular dichroism. Chirality. 1997;9:578-82.
[29] Zhang L-B, Ji J, Lei C, Wang H-Y, Zhao Q-S, Hou A-J. Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa. J Nat Prod. 2012;75(4):699-706.
[30] Han XH, Hong SS, Jin Q, Li D, Kim HK, Lee J, Kwon SH, Lee D, Lee CK, Lee MK, Hwang BY. Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata. J Nat Prod. 2009;72:164-7.
[31] Yap SP, Shen P, Butler MS, Gong Y, Loy CJ, Yong EL. New estrogenic prenylflavone from Epimedium brevicornum inhibits the growth of breast cancer cells. Planta Med. 2005;71:114-9.
[32] Gerards M, Snatzke G. Circular dichroism, XCIII’ determination of the absolute configuration of alcohols, olefins, epoxides, and ethers from the CD of their “in suit” complexes with [Rh₂(O₂CCF₃)₄]. Tetrahedron Asymmetr. 1990;1:221-36.
[33] Meng LH, Awakawa T, Li XM, Quan Z, Yang SQ, Wang BG, Abe I. Discovery of (±)-penindolenes reveals an unusual indole ring cleavage pathway catalyzed by P450 monooxygenase. Angew Chem Int Ed. 2024. https://doi.org/10.1002/anie.202403963.
[34] Li F-F, Sun Q, Wang D, Liu S, Lin B, Liu C-T, Li L-Z, Huang X-X, Song S-J. Chiral separation of cytotoxic flavan derivatives from Daphne giraldii. J Nat Prod. 2016;79(9):2236-42.
[35] Finefield JM, Sherman DH, Kreitman M, Williams RM. Enantiomeric natural products: occurrence and biogenesis. Angew Chem Int Ed. 2012;51(20):4802-36.
[36] Tiritan ME, Fernandes C, Maia AS, Pinto M, Cass QB. Enantiomeric ratios: why so many notations? J Chromatogr A. 2018;1569:1-7.
[37] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. Gaussian 16 Revision. CT: Wallingford; 2016.
[38] Bruhn T, Schaumlöffel A, Hemberger Y, Pescitelli G. SpecDis version 1.71. Berlin, Germany. 2017.